Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover) episode artwork

EPISODE · Jun 22, 2026 · 34 MIN

Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover)

from Winging It Travel Podcast

Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover)This week on Winging It, I'm sharing a special crossover episode from my other podcast, Taking A Career Break with Katrina McGhee. I really feel our two audiences do crossover, so I am sharing one of our most popular episodes with you. Please check out the rest of the catalogue for everything relating to a career break.Episode 67 - Why You Should Stop Waiting for the “Right Time” to Take a Career Break ShownotesIf you've ever dreamed of taking a career break, travelling the world, changing direction, or simply pressing pause on the life you've built, you've probably told yourself the same thing many of us do:"I'll do it when the timing is right."The truth is, there may never be a perfect time.In this episode, Katrina and I dive into one of the biggest reasons people never take a career break: waiting for the mythical "right time." We explore why life will always present obstacles, why fear often disguises itself as practicality, and how delaying your dreams can lead to years of wondering "what if?"Is there ever a right time to take a career break—or are you just waiting forever?From economic uncertainty and job market fears to internal pressure and workplace guilt, they unpack why it always feels like the wrong time—and why that thinking is keeping you stuck.Katrina introduces the concept of PHOBO (Fear of Becoming Obsolete) and explains how this fear shows up both before and during a career break—often preventing people from fully committing to the change they need.You’ll learn why the “perfect moment” doesn’t exist, how your brain is wired to keep you in survival mode, and what it actually takes to create a good enough time to step away and reset your life.If you’ve been telling yourself “maybe next year” or “once things settle down,” this episode will challenge that narrative—and help you take your first real step toward a career break.Taking A Career Break with Katrina McGheeApple Podcasts - https://podcasts.apple.com/ca/podcast/taking-a-career-break-with-katrina-mcghee/id1772602758Spotify - https://open.spotify.com/show/1lRPigXIghYUw82Eqak0mF?si=b956d5b826df4cf1YouTube - https://www.youtube.com/@TakingaCareerBreakwithKatrinaReady to stop "running on empty" and start running toward a life you actually love?📞Schedule a call with Katrina - ⁠⁠⁠⁠⁠⁠⁠https://kmcgheecoaching.as.me/freeconsult⁠⁠⁠⁠⁠⁠⁠🫶🏼Join the BreakSpace community - ⁠⁠⁠⁠⁠⁠⁠www.gobreakspace.com⁠⁠⁠⁠⁠⁠⁠🎁Order Katrina's book (w/ special bonus!) - ⁠⁠⁠⁠⁠⁠⁠https://www.kmcgheecoaching.com/book⁠⁠⁠⁠⁠⁠⁠Support Winging It Travel PodcastIf you enjoyed this episode:⭐ Leave a 5-star rating or review on your podcast app☕ Support the show at buymeacoffee.com/wingingit🌍 Explore more episodes at wingingittravelpodcast.com✈️ Check out more great travel podcasts at https://voyascape.com📺 Now also on YouTube - https://www.youtube.com/@wingingittravelpodcast⏱️ Timestamps00:00 Introduction – Why this career break episode matters for travellers02:08 Winging It Travel Podcast intro03:47 Welcome to Taking A Career Break with Katrina McGhee04:39 Why do we keep waiting for the "right time"?06:34 The fear of becoming obsolete and falling behind08:13 Is there ever a good economic time to take a break?10:59 Why hard times don't mean you can't make a career break happen13:00 James shares his own fears about timing and entrepreneurship15:27 The "worst time fallacy" explained17:13 Why guilt keeps people stuck in jobs18:52 Break Space: Support for your own career break journey19:28 The target keeps moving – there will always be another excuse22:58 When has life ever truly felt certain?24:39 Planning versus endlessly postponing your dreams26:23 Why the perfect moment doesn't exist27:15 How fear of falling behind keeps you in survival mode29:32 Building the bridge before taking the leap31:05 Stop waiting and start making your career break happen32:17 Final thoughts and outro--------------------------------------------------------------Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠Voyascape: Travel Podcast Network - https://voyascape.com/Winging It Travel Podcast - Website--------------------------------------------------------------Winging It Travel Podcast CreditsHost/Producer/Creator/Composer/Editor - James HammondContact me - [email protected] or [email protected] Media - follow me on:InstagramTikTok Facebook--------------------------------------------------------------Affiliate Links If you click one of the below to book something, I get a tiny commission, which helps the podcast.Book Flights with Skyscanner - HereUse Revolut Travel Card - HereBook Hostels With Hostelworld - HereBooking.com - HereBook Experiences With Viator - HereDiscovery Car Hire - HereBook Buses With Busbud - HereBook Trains With Trainline - HereTravel Insurance with SafetyWing - HereBook Flights With Expedia Canada - Here--------------------------------------------------------------Thanks for supporting me and the podcast!Cheers James.Mentioned in this episode:Check out all of our other travel podcasts from around the worldThis podcast is part of Voyascape, a podcast network that brings together the world's best travel podcasts. You can find all of our podcasts from around the world at Voyascape.com. If you are interested in advertising or sponsored content on any of our shows you can find out more at the link below.Voyascape Podcast Network

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This episode was published on June 22, 2026.

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Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover)This week on Winging It, I'm sharing a special crossover episode from my other podcast, Taking A Career Break with Katrina McGhee....

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